BRPI0616146A2 - derivados benzotiazol ciclobutil amina e seu uso como ligantes dos receptores de histamina-3 - Google Patents

derivados benzotiazol ciclobutil amina e seu uso como ligantes dos receptores de histamina-3 Download PDF

Info

Publication number: BRPI0616146A2
Authority: BR; Brazil
Prior art keywords: cyclobutyl; trans; benzothiazol; benzothiazole; piperidin
Prior art date: 2005-09-22

Application number

BRPI0616146-4A

Other languages

English (en)

Portuguese (pt)

Inventor

Marlon D Cowart

Minghua Sun

Chen Zhao

Guo Zhu Zheng

Original Assignee

Abbott Lab

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2005-09-22

Filing date

2006-09-19

Publication date

2011-06-07

2006-09-19 Application filed by Abbott Lab filed Critical Abbott Lab

2011-06-07 Publication of BRPI0616146A2 publication Critical patent/BRPI0616146A2/pt

Links

-1 benzothiazole cyclobutyl amine derivatives Chemical class 0.000 title claims description 360
239000011230 binding agent Substances 0.000 title description 11
IOJUPLGTWVMSFF-UHFFFAOYSA-N cyclobenzothiazole Natural products C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 title description 6
150000001875 compounds Chemical class 0.000 claims abstract description 497
238000000034 method Methods 0.000 claims abstract description 241
239000008194 pharmaceutical composition Substances 0.000 claims abstract description 12
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 140
125000000217 alkyl group Chemical group 0.000 claims description 69
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 65
229910052739 hydrogen Inorganic materials 0.000 claims description 52
239000001257 hydrogen Substances 0.000 claims description 51
AAILEWXSEQLMNI-UHFFFAOYSA-N 1h-pyridazin-6-one Chemical compound OC1=CC=CN=N1 AAILEWXSEQLMNI-UHFFFAOYSA-N 0.000 claims description 43
239000002253 acid Substances 0.000 claims description 43
125000000623 heterocyclic group Chemical group 0.000 claims description 42
150000002431 hydrogen Chemical group 0.000 claims description 41
125000003118 aryl group Chemical group 0.000 claims description 39
125000000753 cycloalkyl group Chemical group 0.000 claims description 36
229910052757 nitrogen Inorganic materials 0.000 claims description 35
RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 31
125000003545 alkoxy group Chemical group 0.000 claims description 31
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 30
229910003827 NRaRb Inorganic materials 0.000 claims description 25
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 25
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 25
125000004093 cyano group Chemical group *C#N 0.000 claims description 23
230000000694 effects Effects 0.000 claims description 23
150000001412 amines Chemical class 0.000 claims description 21
208000035475 disorder Diseases 0.000 claims description 21
150000002148 esters Chemical class 0.000 claims description 21
125000001424 substituent group Chemical group 0.000 claims description 21
125000002252 acyl group Chemical group 0.000 claims description 19
125000004414 alkyl thio group Chemical group 0.000 claims description 19
229910052736 halogen Inorganic materials 0.000 claims description 19
150000002367 halogens Chemical class 0.000 claims description 19
125000002768 hydroxyalkyl group Chemical group 0.000 claims description 19
150000003839 salts Chemical class 0.000 claims description 19
229910052799 carbon Inorganic materials 0.000 claims description 18
NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 17
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 17
125000001188 haloalkyl group Chemical group 0.000 claims description 17
125000004433 nitrogen atom Chemical group N* 0.000 claims description 17
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 16
125000006574 non-aromatic ring group Chemical group 0.000 claims description 16
229920002472 Starch Chemical group 0.000 claims description 14
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
125000001072 heteroaryl group Chemical group 0.000 claims description 14
235000019698 starch Nutrition 0.000 claims description 14
125000003342 alkenyl group Chemical group 0.000 claims description 13
125000002947 alkylene group Chemical group 0.000 claims description 13
150000001408 amides Chemical class 0.000 claims description 13
229910052760 oxygen Inorganic materials 0.000 claims description 13
UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-UHFFFAOYSA-N 0.000 claims description 13
125000004423 acyloxy group Chemical group 0.000 claims description 12
125000005083 alkoxyalkoxy group Chemical group 0.000 claims description 12
239000008107 starch Chemical group 0.000 claims description 12
229910052717 sulfur Inorganic materials 0.000 claims description 12
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
125000004438 haloalkoxy group Chemical group 0.000 claims description 11
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 11
201000000980 schizophrenia Diseases 0.000 claims description 11
125000000676 alkoxyimino group Chemical group 0.000 claims description 10
125000005138 alkoxysulfonyl group Chemical group 0.000 claims description 10
TXWOGHSRPAYOML-UHFFFAOYSA-N cyclobutanecarboxylic acid Chemical compound OC(=O)C1CCC1 TXWOGHSRPAYOML-UHFFFAOYSA-N 0.000 claims description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 10
125000003396 thiol group Chemical class [H]S* 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 9
125000003226 pyrazolyl group Chemical group 0.000 claims description 9
125000004076 pyridyl group Chemical group 0.000 claims description 9
125000000714 pyrimidinyl group Chemical group 0.000 claims description 9
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 8
125000000304 alkynyl group Chemical group 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 8
239000003937 drug carrier Substances 0.000 claims description 8
125000001425 triazolyl group Chemical group 0.000 claims description 8
125000002393 azetidinyl group Chemical group 0.000 claims description 7
NIPZZXUFJPQHNH-UHFFFAOYSA-N pyrazine-2-carboxylic acid Chemical compound OC(=O)C1=CN=CC=N1 NIPZZXUFJPQHNH-UHFFFAOYSA-N 0.000 claims description 7
125000001422 pyrrolinyl group Chemical group 0.000 claims description 7
125000000168 pyrrolyl group Chemical group 0.000 claims description 7
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 7
125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
ABXPYCIUPKSNPM-XSRFYTQQSA-N 6-bromo-2-[3-[(2r)-2-methylpyrrolidin-1-yl]cyclobutyl]-1,3-benzothiazole Chemical compound C[C@@H]1CCCN1C1CC(C=2SC3=CC(Br)=CC=C3N=2)C1 ABXPYCIUPKSNPM-XSRFYTQQSA-N 0.000 claims description 6
206010010904 Convulsion Diseases 0.000 claims description 6
125000004069 aziridinyl group Chemical group 0.000 claims description 6
230000007278 cognition impairment Effects 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000004193 piperazinyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000003373 pyrazinyl group Chemical group 0.000 claims description 6
125000002098 pyridazinyl group Chemical group 0.000 claims description 6
125000005494 pyridonyl group Chemical group 0.000 claims description 6
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
YUXZYOIYOWPNBW-JEYLPNPQSA-N 6-(2,4-dimethoxypyrimidin-5-yl)-2-[3-[(2s)-2-methylpyrrolidin-1-yl]cyclobutyl]-1,3-benzothiazole Chemical compound COC1=NC(OC)=NC=C1C1=CC=C(N=C(S2)C3CC(C3)N3[C@H](CCC3)C)C2=C1 YUXZYOIYOWPNBW-JEYLPNPQSA-N 0.000 claims description 5
208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 5
YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Natural products C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 5
125000003725 azepanyl group Chemical group 0.000 claims description 5
125000004541 benzoxazolyl group Chemical group O1C(=NC2=C1C=CC=C2)* 0.000 claims description 5
208000010877 cognitive disease Diseases 0.000 claims description 5
BAVYZALUXZFZLV-UHFFFAOYSA-N mono-methylamine Natural products NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 claims description 5
208000011580 syndromic disease Diseases 0.000 claims description 5
125000004485 2-pyrrolidinyl group Chemical group [H]N1C([H])([H])C([H])([H])C([H])([H])C1([H])* 0.000 claims description 4
208000024827 Alzheimer disease Diseases 0.000 claims description 4
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 claims description 4
OVDHIDWLHHCHDB-CTYIDZIISA-N C1CN(C1)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 Chemical compound C1CN(C1)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 OVDHIDWLHHCHDB-CTYIDZIISA-N 0.000 claims description 4
BNNXTGQYDDNTHG-KOMQPUFPSA-N C1[C@@H](C[C@H]1c1nc2ccc(cc2s1)-c1cncnc1)N1CCCC1 Chemical compound C1[C@@H](C[C@H]1c1nc2ccc(cc2s1)-c1cncnc1)N1CCCC1 BNNXTGQYDDNTHG-KOMQPUFPSA-N 0.000 claims description 4
FPIOZVJJQMCVFX-JCNLHEQBSA-N C1[C@@H](C[C@H]1c1nc2ccc(cc2s1)-c1cncnc1)N1CCCCC1 Chemical compound C1[C@@H](C[C@H]1c1nc2ccc(cc2s1)-c1cncnc1)N1CCCCC1 FPIOZVJJQMCVFX-JCNLHEQBSA-N 0.000 claims description 4
GYWCHNSDHIJRPI-ATZDWAIDSA-N C[C@@H]1CCCN1[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1ccc(C)nc1C Chemical compound C[C@@H]1CCCN1[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1ccc(C)nc1C GYWCHNSDHIJRPI-ATZDWAIDSA-N 0.000 claims description 4
RINYBFJVYSKATO-XIRDDKMYSA-N FC[C@@H]1CCCN1[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 Chemical compound FC[C@@H]1CCCN1[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 RINYBFJVYSKATO-XIRDDKMYSA-N 0.000 claims description 4
208000026139 Memory disease Diseases 0.000 claims description 4
CLVPOZCCNGMQSL-AULYBMBSSA-N N1(CCCCC1)[C@@H]1C[C@H](C1)C=1SC2=C(N1)C=CC(=C2)N Chemical compound N1(CCCCC1)[C@@H]1C[C@H](C1)C=1SC2=C(N1)C=CC(=C2)N CLVPOZCCNGMQSL-AULYBMBSSA-N 0.000 claims description 4
TUQJMUVOHBTCKY-KOMQPUFPSA-N O=c1cccnn1-c1ccc2nc(sc2c1)[C@H]1C[C@@H](C1)N1CCCCC1 Chemical compound O=c1cccnn1-c1ccc2nc(sc2c1)[C@H]1C[C@@H](C1)N1CCCCC1 TUQJMUVOHBTCKY-KOMQPUFPSA-N 0.000 claims description 4
AIHXBSPGERDVJQ-SAABIXHNSA-N OCC1CCN(CC1)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 Chemical compound OCC1CCN(CC1)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1cncnc1 AIHXBSPGERDVJQ-SAABIXHNSA-N 0.000 claims description 4
208000008589 Obesity Diseases 0.000 claims description 4
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208000015802 attention deficit-hyperactivity disease Diseases 0.000 claims description 4
125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 4
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004196 benzothienyl group Chemical group S1C(=CC2=C1C=CC=C2)* 0.000 claims description 4
125000004802 cyanophenyl group Chemical group 0.000 claims description 4
206010013663 drug dependence Diseases 0.000 claims description 4
206010015037 epilepsy Diseases 0.000 claims description 4
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 4
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 4
125000002883 imidazolyl group Chemical group 0.000 claims description 4
125000003453 indazolyl group Chemical group N1N=C(C2=C1C=CC=C2)* 0.000 claims description 4
125000001041 indolyl group Chemical group 0.000 claims description 4
125000001786 isothiazolyl group Chemical group 0.000 claims description 4
125000000842 isoxazolyl group Chemical group 0.000 claims description 4
235000020824 obesity Nutrition 0.000 claims description 4
125000002971 oxazolyl group Chemical group 0.000 claims description 4
IIVUJUOJERNGQX-UHFFFAOYSA-N pyrimidine-5-carboxylic acid Chemical compound OC(=O)C1=CN=CN=C1 IIVUJUOJERNGQX-UHFFFAOYSA-N 0.000 claims description 4
208000011117 substance-related disease Diseases 0.000 claims description 4
125000003831 tetrazolyl group Chemical group 0.000 claims description 4
125000004306 triazinyl group Chemical group 0.000 claims description 4
JCZAVVUIFWZMQI-UHFFFAOYSA-N 1h-thieno[2,3-d]imidazole Chemical compound N1C=NC2=C1C=CS2 JCZAVVUIFWZMQI-UHFFFAOYSA-N 0.000 claims description 3
VDVJQFLGCFFFBP-UHFFFAOYSA-N 2,3-dihydropyrrole-1-carboxylic acid Chemical compound OC(=O)N1CCC=C1 VDVJQFLGCFFFBP-UHFFFAOYSA-N 0.000 claims description 3
HUOAEBFRBWKTQE-UHFFFAOYSA-N 2-(2-methoxypyrimidin-5-yl)-1,3-benzothiazole Chemical compound C1=NC(OC)=NC=C1C1=NC2=CC=CC=C2S1 HUOAEBFRBWKTQE-UHFFFAOYSA-N 0.000 claims description 3
CLVPOZCCNGMQSL-UHFFFAOYSA-N 2-(3-piperidin-1-ylcyclobutyl)-1,3-benzothiazol-6-amine Chemical compound S1C2=CC(N)=CC=C2N=C1C(C1)CC1N1CCCCC1 CLVPOZCCNGMQSL-UHFFFAOYSA-N 0.000 claims description 3
CVEBXWMUCRDRQP-UHFFFAOYSA-N 2-(3-piperidin-1-ylcyclobutyl)-n-pyrimidin-5-yl-1,3-benzothiazol-6-amine Chemical compound C1C(N2CCCCC2)CC1C(SC1=C2)=NC1=CC=C2NC1=CN=CN=C1 CVEBXWMUCRDRQP-UHFFFAOYSA-N 0.000 claims description 3
UATBYRPUSAQAML-UHFFFAOYSA-N 6-pyrimidin-5-yl-2-[3-(pyrrolidin-1-ylmethyl)cyclobutyl]-1,3-benzothiazole Chemical compound C1CCCN1CC(C1)CC1C(SC1=C2)=NC1=CC=C2C1=CN=CN=C1 UATBYRPUSAQAML-UHFFFAOYSA-N 0.000 claims description 3
UGYKZEQGXFGOFK-UMSPYCQHSA-N Brc1ccc2nc(sc2c1)[C@H]1C[C@@H](C1)N1CCOCC1 Chemical compound Brc1ccc2nc(sc2c1)[C@H]1C[C@@H](C1)N1CCOCC1 UGYKZEQGXFGOFK-UMSPYCQHSA-N 0.000 claims description 3
NLZOPDAUVGPKSU-IYARVYRRSA-N CC(C)N(C)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1ccc(C)nc1C Chemical compound CC(C)N(C)[C@H]1C[C@@H](C1)c1nc2ccc(cc2s1)-c1ccc(C)nc1C NLZOPDAUVGPKSU-IYARVYRRSA-N 0.000 claims description 3
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KVBGRLIOEMFCGG-SHTZXODSSA-N COc1ncc(-c2ccc3nc(sc3c2)[C@H]2C[C@@H](C2)N2CCCC2)c(OC)n1 Chemical compound COc1ncc(-c2ccc3nc(sc3c2)[C@H]2C[C@@H](C2)N2CCCC2)c(OC)n1 KVBGRLIOEMFCGG-SHTZXODSSA-N 0.000 claims description 3
YUXZYOIYOWPNBW-FVQBIDKESA-N COc1ncc(-c2ccc3nc(sc3c2)[C@H]2C[C@@H](C2)N2CCC[C@H]2C)c(OC)n1 Chemical compound COc1ncc(-c2ccc3nc(sc3c2)[C@H]2C[C@@H](C2)N2CCC[C@H]2C)c(OC)n1 YUXZYOIYOWPNBW-FVQBIDKESA-N 0.000 claims description 3
CGEXIEBOQFSPNA-QBIRGWOPSA-N COc1ncc(-c2ccc3sc(nc3c2)[C@H]2C[C@@H](C2)N2CCCC2C)c(OC)n1 Chemical compound COc1ncc(-c2ccc3sc(nc3c2)[C@H]2C[C@@H](C2)N2CCCC2C)c(OC)n1 CGEXIEBOQFSPNA-QBIRGWOPSA-N 0.000 claims description 3
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125000001981 tert-butyldimethylsilyl group Chemical group [H]C([H])([H])[Si]([H])(C([H])([H])[H])[*]C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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CBXCPBUEXACCNR-UHFFFAOYSA-N tetraethylammonium Chemical compound CC[N+](CC)(CC)CC CBXCPBUEXACCNR-UHFFFAOYSA-N 0.000 description 1
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BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical compound C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 description 1
238000002560 therapeutic procedure Methods 0.000 description 1
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125000000335 thiazolyl group Chemical group 0.000 description 1
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VNNLHYZDXIBHKZ-UHFFFAOYSA-N thiophene-2-sulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CS1 VNNLHYZDXIBHKZ-UHFFFAOYSA-N 0.000 description 1
210000001685 thyroid gland Anatomy 0.000 description 1
239000012485 toluene extract Substances 0.000 description 1
JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
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QQJLHRRUATVHED-UHFFFAOYSA-N tramazoline Chemical compound N1CCN=C1NC1=CC=CC2=C1CCCC2 QQJLHRRUATVHED-UHFFFAOYSA-N 0.000 description 1
229960001262 tramazoline Drugs 0.000 description 1
238000000844 transformation Methods 0.000 description 1
TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
STMPXDBGVJZCEX-UHFFFAOYSA-N triethylsilyl trifluoromethanesulfonate Chemical compound CC[Si](CC)(CC)OS(=O)(=O)C(F)(F)F STMPXDBGVJZCEX-UHFFFAOYSA-N 0.000 description 1
150000008648 triflates Chemical class 0.000 description 1
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
JBWKIWSBJXDJDT-UHFFFAOYSA-N triphenylmethyl chloride Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(Cl)C1=CC=CC=C1 JBWKIWSBJXDJDT-UHFFFAOYSA-N 0.000 description 1
229910052722 tritium Inorganic materials 0.000 description 1
210000004881 tumor cell Anatomy 0.000 description 1
239000010681 turmeric oil Substances 0.000 description 1
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150000003672 ureas Chemical class 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
238000002061 vacuum sublimation Methods 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
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BRPI0616146-4A 2005-09-22 2006-09-19 derivados benzotiazol ciclobutil amina e seu uso como ligantes dos receptores de histamina-3 BRPI0616146A2 (pt)

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US71951605P	2005-09-22	2005-09-22
US60/719,516		2005-09-22
US11/518,132		2006-09-08
US11/518,132 US7576110B2 (en)	2005-09-22	2006-09-08	Benzothiazole cyclobutyl amine derivatives
PCT/US2006/036422 WO2007038074A1 (en)	2005-09-22	2006-09-19	Benzothiazole cyclobutyl amine derivatives and their use as histamine-3 receptors ligands

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US (2)	US7576110B2 (sr)
EP (2)	EP1926729B1 (sr)
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AT (1)	ATE538119T1 (sr)
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BR (1)	BRPI0616146A2 (sr)
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NZ586399A (en) *	2008-01-24	2011-12-22	Ucb Pharma Sa	Compounds comprising a cyclobutoxy group
KR100986433B1 (ko)	2008-05-30	2010-10-08	현대자동차주식회사	전동식 파워스티어링 시스템
US9186353B2 (en) *	2009-04-27	2015-11-17	Abbvie Inc.	Treatment of osteoarthritis pain
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EP3634953B1 (en)	2017-06-05	2024-01-03	PTC Therapeutics, Inc.	Compounds for treating huntington's disease
JP7399870B2 (ja)	2018-03-27	2023-12-18	ピーティーシーセラピューティクス，インコーポレイテッド	ハンチントン病を処置するための化合物
KR20210038845A (ko)	2018-06-27	2021-04-08	피티씨 테라퓨틱스, 인크.	헌팅턴병 치료를 위한 헤테로아릴 화합물
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2006
- 2006-09-08 US US11/518,132 patent/US7576110B2/en active Active
- 2006-09-19 MY MYPI20080763A patent/MY146028A/en unknown
- 2006-09-19 SI SI200631280T patent/SI1926729T1/sl unknown
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- 2006-09-19 AT AT06814914T patent/ATE538119T1/de active
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- 2006-09-19 ES ES06814914T patent/ES2378197T3/es active Active
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- 2006-09-19 KR KR1020087009662A patent/KR20080050628A/ko not_active Ceased
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- 2006-09-21 TW TW095135007A patent/TWI393717B/zh not_active IP Right Cessation
2008
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2009
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Also Published As

Publication number	Publication date
CR9822A (es)	2008-08-01
ATE538119T1 (de)	2012-01-15
EP1926729B1 (en)	2011-12-21
TW200745098A (en)	2007-12-16
IL190350A (en)	2013-08-29
AU2006295065A1 (en)	2007-04-05
HRP20120251T1 (hr)	2012-07-31
EP1926729A1 (en)	2008-06-04
WO2007038074A1 (en)	2007-04-05
AU2006295065B2 (en)	2012-03-08
CY1112727T1 (el)	2016-02-10
RS52231B (sr)	2012-10-31
ZA200802508B (en)	2012-09-26
JP2009508957A (ja)	2009-03-05
AU2006295065C1 (en)	2012-11-22
ES2378197T3 (es)	2012-04-09
NO20081905L (no)	2008-06-23
SI1926729T1 (sl)	2012-04-30
HRP20080174A2 (hr)	2008-12-31
NZ566834A (en)	2011-08-26
RU2008115313A (ru)	2009-10-27
US8592467B2 (en)	2013-11-26
PT1926729E (pt)	2012-03-27
IL190350A0 (en)	2009-09-22
PL1926729T3 (pl)	2012-05-31
EP2386556A1 (en)	2011-11-16
TWI393717B (zh)	2013-04-21
DK1926729T3 (da)	2012-03-19
ECSP088326A (es)	2008-04-28
KR20080050628A (ko)	2008-06-09
US20090326222A1 (en)	2009-12-31
MY146028A (en)	2012-06-15
MY150990A (en)	2014-03-31
EP2386556B1 (en)	2013-10-23
US7576110B2 (en)	2009-08-18
US20070066588A1 (en)	2007-03-22
HK1118291A1 (en)	2009-02-06
CA2623252A1 (en)	2007-04-05

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2014-05-06	B25A	Requested transfer of rights approved	Owner name: ABBVIE INC. (US)
2015-07-21	B08F	Application dismissed because of non-payment of annual fees [chapter 8.6 patent gazette]	Free format text: REFERENTE A 9A ANUIDADE.
2015-11-24	B08K	Patent lapsed as no evidence of payment of the annual fee has been furnished to inpi [chapter 8.11 patent gazette]	Free format text: EM VIRTUDE DO ARQUIVAMENTO PUBLICADO NA RPI 2324 DE 21-07-2015 E CONSIDERANDO AUSENCIA DE MANIFESTACAO DENTRO DOS PRAZOS LEGAIS, INFORMO QUE CABE SER MANTIDO O ARQUIVAMENTO DO PEDIDO DE PATENTE, CONFORME O DISPOSTO NO ARTIGO 12, DA RESOLUCAO 113/2013.

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